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Business Casual Superstar #508: Dress It Up!

Written By: humarashid - Sep• 14•15

I’m back. I missed this thing. I missed doing business casual outfits like I used to back when I was in law school. I’m obviously an attorney now, so my focus has shifted a bit: I’m still into business casual, obviously, but I’m also into court wear. And the best thing is when you can easily switch between the two … and possibly switch the same outfit easily to something to wear out at night, too.

So the next few posts in this series will be outfits that are easily convertible: wear it to court, wear it around the (business casual) office, wear it out at night.

In order to keep it under $100, I’m often going to presume that you have a basic black blazer, a cardigan, things like that. I will of course be providing links to some of those basics, but I’m playing the $100 a little fast and loose, because a black blazer is something most of us already have in our closet (but if not, never fear! I’ll provide some).

Here we go.

I love, love, love dresses. I love them. I wear them with and without pantyhose, with stockings, with opaque tights, with leggings, whatever. I’m all about dresses. BECAUSE THEY AREN’T PANTS.

Here’s my thing: I fucking hate pants. Like, no, fuck pants. They are the worst. And if you roll out of bed, shower, and throw on a dress with a cardigan and some flats, you just managed to get dressed in about 2 minutes, and you look like you put way more thought into it than you did. And I’m all about looking like I put more thought into things than I actually did, because I don’t have all that many thoughts to spare, guys.


Oh, whatever, you know what I mean.

So here we go:

BCS 508

Isn’t this nuts? This whole outfit for under $50? Ok, bear with me while I explain this shit.

Star Vixen Bar Back Dress: $8.84

Romwe Round Neck Cropped Blazer: $14.67

Qupid Dress Pump: $17.85

I found this dress on Amazon. I never would have thought to buy clothing on Amazon, but for the past two years, BobBlahBlawg has been randomly IMing me and being like, “What do you think of these shoes?” and he’ll send me Amazon links to men’s shoes. And I mean I can’t fault the guy; he’s got good taste. But because of that, I’ve kind of been able to wrap my mind around buying clothes on Amazon.

So the dress is from Amazon. It’s knee-length, and it’s not super booby, so it’ll be fine for court, especially under a blazer. It’s got a barred back, which you can’t see in this pic, but you can if you click on the link and go to Amazon.

It’s not indecent, but you’re not going to be walking into court like that unless you WANT people to think that you won that Motion to Dismiss for reasons other than your stellar legal arguments. (Is that slut-shamey? Help me out. I don’t want to be slut-shamey.)

Naturally it has to be paired with a blazer. I’m super biased here, because I LOVE cropped and/or fitted blazer. I’m a small girl: I’m only 5’1″ and if I wear normal boxy blazers I look like I’m swimming in fabric. I’ve already gained some weight since law school, and I do not need to look even fatter. I mean, it’s bad enough that I’ve been forced to realize that I can no longer eat pizza and ice cream for a literal week without gaining a literal pound. (UGH. WHY CRUEL WORLD WHY.)

So I go with fitted or cropped blazers. And I like this one. I’d totally wear it to court. I’d look great. (I have blue and silver blazers just like this, so it’s not a stretch – I really would wear this to court.) If you want a more normal blazer, consider this long-sleeve black blazer from JCPenney for $25, currently on sale. Everyone’s tastes are different, and everyone’s bodies are different. Cropped/fitted blazers might fit you in a way that doesn’t make you comfortable. So throw on a more traditional, looser blazer if that’s your scene.

The shoes are also from Amazon. I should just do Amazon-only outfits from now on because I swear they have everything. They tend to run a half size too small, according to the review, so I went with the price point for a 7.5 shoe, since I’m a 7. They’re just normal black pumps, and I threw them in kind of as an afterthought, because I figure most of us have black leather pumps in our closet anyway and don’t need to buy these.

Actually, I no longer have black leather heels. Mine were looking ROUGH so I got rid of them. I tend to walk hard and fast. My heel strikes the concrete pavement hard and I walk quickly, so the tips of my heel gets worn down quick. Sometimes I step in those stupid grates and nick the leather. I am a literal disaster. I am not one of those poised, graceful, gazelle-like creatures that can float down Dearborn in the Loop looking like she just stepped out of a White House Black Market catalog.

No. If you see me walking down Dearborn, I am striding purposely toward the Dirksen Federal Building, running through crosswalks with 3 seconds left on the orange timer, sucking down as much of my iced caramel coffee as I can before I dump it in one of the garbage cans outside the building and barrel through the revolving doors because those fuckers start on TIME.

I am hardly a vision of feminine loveliness when I’m walking down the street to get to court (or ever, really). So my heels get roughed up quick, which is why I wear flats everywhere, because fuck that.

Ugh, I need to buy black heels.

ANYWAY. This outfit pictured above will carry you through your morning court call, easy. But what about when you get back to the office?

Ditch the heels for these black flats, $12 at MyHabit.

black flat

They’re comfortable and easy on your feet, and you can flit about the office for the rest of the day in comfort. (The soles might be kind of thin, because they’re rather discounted in price, so be cautious.) If I’m wearing shoes at all in the office, I am wearing flats or sandals. (No, I’m serious, I’m often just not wearing shoes in the office because fuck shoes.)

Also, you don’t want to hang out in a blazer around the office, do you? Unless a client is coming in, I’m walking around in just my dress, to be honest. But when we do have a client meeting, I quickly grab either my blazer or a sweater that I keep at the office. That’s what you should do, too: ditch the blazer for this loose, flowy, open-front grey cardigan for $20.50 on, you guessed it, Amazon.


Look at how cute! I love flowy, draped cardigans. And cardigans in general. Like the blazer, it hides the slightly racy back very well, and you still look cute and professional and most importantly, comfortable.

But what happens when the clock hits 5 (or 6, or 7) and it’s time to get your ass on out of there and do something fun with your girlfriends (or, my favorite, by myself)? You want to go out to dinner or for drinks or coffee or whatever, and you don’t want to look like you just came from work … even though you just came from work.

Ditch the sweater and the blazer, forget the pumps and flats, and throw on something strappy, like these silver sandals I found at Nordstrom Rack for $10.

silver heels

Yikes, you could put an eye out with those. But they’re so pretty and strappy. The strap on top would keep me from dangling them off my feet, which I love to do maybe as a nervous or bored tick, but whatever. Throw them on and go have fun.

And the best part?

Even if you buy every single thing I posted on here (but pick one blazer – either the fitted or the normal one, not both!) the total price is still at around $92. For everything! Court to office to a night out! YAY! I outdid myself! I love that feeling.

Anyway, there we have it: an outfit that can transition from court to the business casual office and to the bar or brewery or restaurant or lounge you find yourself at afterwards. Whatever, I’m not your mom, I don’t care what you do. Go stick your tongue down some random’s throat for all I care. (And have fun!)

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